A growing area of research surrounds the role principals play in the retention of teachers amidst the lack of systemic and state policies needed to retain them, especially in Title I schools where student experience with teacher turnover is disproportionate to their non-Title I counterparts (Boyd et al., 2011; Nguyen, 2021). Principals are uniquely positioned to provide instructional guidance and organizational support for teachers to be set up for success despite the unpredictable wake of state policy or school contextual factors (Wallace Foundation, 2013). This exploratory qualitative study aimed to explore the perceptions of teachers working in Title I high schools about how principals influenced their decisions to remain or leave their schools and their overall dedication to the education profession. The findings emphasize the critical role that principals’ leadership styles—particularly the balance between transactional and transformative approaches—play in shaping teachers’ retention decisions and overall job satisfaction. This study suggests that teachers in Title I high schools value principals who are visible, relatable, and invested in fostering a supportive and stable school environment. Principals who demonstrate a commitment to both organizational efficiency and teacher empowerment contribute positively to teachers' decisions to remain in their schools. Findings indicate that principals have more influence over teachers moving from school to school rather than leaving the profession altogether.